Issue 16, 2022

19F-centred NMR analysis of mono-fluorinated compounds

Abstract

Addressing limitations of the existing NMR techniques for the structure determination of mono-fluorinated compounds, we have developed methodology that uses 19F as the focal point of this process. The proposed 19F-centred NMR analysis consists of a complementary set of broadband, phase-sensitive NMR experiments that utilise the substantial sensitivity of 19F and its far reaching couplings with 1H and 13C to obtain a large number of NMR parameters. The assembled 1H, 13C and 19F chemical shifts, values of JHF, JHH, and JFC coupling constants and the size of 13C induced 19F isotopic shifts constitute a rich source of information that enables structure elucidation of fluorinated moieties and even complete structures of molecules. Here we introduce the methodology, provide a detailed description of each NMR experiment and illustrate their interpretation using 3-fluoro-3-deoxy-D-glucose. This novel approach performs particularly well in the structure elucidation of fluorinated compounds embedded in complex mixtures, eliminating the need for compound separation or use of standards to confirm the structures. It represents a major contribution towards the analysis of fluorinated agrochemicals and (radio)pharmaceuticals at any point during their lifetime, including preparation, use, biotransformation and biodegradation in the environment. The developed methodology can also assist with the investigations of the stability of fluoroorganics and their pharmacokinetics. Studies of reaction mechanisms using fluorinated molecules as convenient reporters of these processes, will also benefit.

Graphical abstract: 19F-centred NMR analysis of mono-fluorinated compounds

Supplementary files

Article information

Article type
Paper
Submitted
02 נוב 2021
Accepted
15 מרץ 2022
First published
30 מרץ 2022
This article is Open Access
Creative Commons BY license

RSC Adv., 2022,12, 10062-10070

19 F-centred NMR analysis of mono-fluorinated compounds

A. J. R. Smith, R. York, D. Uhrín and N. G. A. Bell, RSC Adv., 2022, 12, 10062 DOI: 10.1039/D1RA08046F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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